Compound A, C8H11NO, smells as if it might have been isolated from an extract of dirty socks.

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Compound A, C8H11NO, smells as if it might have been isolated from an extract of dirty socks. This compound can be resolved into enantiomers and it dissolves in 5% aqueous HCl. Oxidation of A with concentrated HNO3, and heat gives nicotinic acid (3-pyridinecarboxylic acid; see Eq. 25.26.) When A reacts with CrO3, in pyridine, compound B (C8H9NO) is obtained. Compound B, when treated with dilute NaOD in D2O, incorporates five deuterium atoms per molecule. Identify A, and explain your reasoning.
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